Methyl iodide → HCID 70109935, compound

HRID 1290722Notes

Reaction equation

HRID 1290722 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H-].[Na+].[CH:11]1([N:17]=[C:18]=[S:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH3:20]I>CN(C=O)C.O>[CH:11]1([NH:17][C:18]([S:19][CH3:20])=[C:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7764Ethyl cyanoacetateHCID 14289Cyclohexyl isothiocyanateHCID 24758Sodium hydride

Product 1

HCID 70109935HCID 70109935, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl cyanoacetate (2.07 g, 18.3 mmol) in DMF (40 ml) was added under ice-cooling sodium hydride (0.77 g, 19.2 mmol). After stirring for one hour, cyclohexyl isothiocyanate (2.59 g, 18.3 mmol) was added dropwise. After stirring under ice-cooling for 1.5 hours, methyl iodide (2.60 g, 18.3 mmol) was added dropwise. After stirring at room temperature for 15 hours, water (400 ml) was added to the reaction mixture, which was then extracted with ethyl acetate (100 ml×2). The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a yellow oily substance (4.76 g) from the fraction from hexane-ethyl acetate (4/1). Yield=97%.

Workup

  1. stirringAfter stirring under ice-
  2. temperaturecooling for 1.5 hours
  3. stirringAfter stirring at room temperature for 15 hours
  4. extractionwas then extracted with ethyl acetate (100 ml×2)
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-664b0bf05a7941aab5574a9f68f4bc18
Source dataset
uspto-grants-1998_05
Patent number
US05753654

Reaction notes

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